THE OMNI SHOW

Jamie Thinglestad: I tend to think that there's, you got to look at the system, you got to look at the tools and the stuff in the system as three different components and make sure that when you're trying to solve or improve, that you're not trying to solve system problems with the tool. The fact that the stuff is not attractive to you, it's not interesting, don't try to solve that by changing your tool. Thinking of those as very different things is important.

Andrew J. Mason: You're listening to The Omni Show where we connect with the amazing community surrounding The Omni Group's award-winning products. My name's Andrew J. Mason, and today we learn how Jamie Thingelstad uses OmniFocus.

Andrew J. Mason: Well, welcome everybody to this episode of the Omni Show. My name's Andrew J. Mason, and I'm curious about have you ever been interested in how a CTO might manage their lives using software like OmniFocus? And today we really get to dive into that world with Jamie Thingelstad. He's the Senior Vice President and Chief Technology Officer of SPS Commerce, and we are super excited and very honored to have him here with us today. Jamie, thank you for joining us.

Jamie Thinglestad: Well, thank you for having me, Andrew.

Andrew J. Mason: I know I just said a mouthful with Senior Vice President, Chief Technology Officer. How would you share that role in, you have a little bit longer than the elevator pitch, but cocktail party kind of style conversation. Somebody says, "Hey, what do you do for a living?" How do you answer that question?

Jamie Thinglestad: Well, I lead the technology functions for SPS Commerce, and that includes things like building and supporting our products, building out our retail network, making sure that our cybersecurity program is executing, making sure that everything all the way to individual employees' laptops are functioning and that everybody's able to get their email and all that. So I joke sometimes that if it plugs into a wall, it probably means that my team in some way engage with it, but we actually engage with a lot of things that also don't plug in too. But fundamentally responsible for making sure that the technology direction of the company is heading in the right direction for where we want to go. And I've been doing that role for almost coming on 30 years, believe it or not, just leading technology teams of different sizes all the way from the team we lead today of several hundred people to teams of several at a startup that is just building a new product and launching it into the market.

Andrew J. Mason: I would imagine that it would be mission-critical that you have some sort of infrastructure to be able to handle the length, breadth and width of requests that happen to come to you in a given week.

Jamie Thinglestad: Right.

Andrew J. Mason: Everything from, Hey, my laptop's not working to, Hey, this whole sector of our company needs to be retooled, or something along those lines.

Jamie Thinglestad: Yes, yes.

Andrew J. Mason: That's just one or two things going on, Jamie geez.

Jamie Thinglestad: I have a lot of things on my waiting for list and a lot of things on my agenda list. My agenda list is by itself spawns into dozens and dozens of sublists.

Andrew J. Mason: Well, I'd love to actually get into that if you'll allow us. Let's first wind back the clock there. Do you have any recollection to the first time that you came across either The Omni Group as a company or OmniFocus as just a software?

Jamie Thinglestad: I do. So it was in 2008 I read David Allen's getting things done, and life was complicated. There was a lot going on and family was growing. It just seemed like there was a lot to do, a lot of plates spinning all at once, and I felt that I needed a better system for managing that. I just felt like I was dropping some things and needed to make sure that I was staying on top of what I wanted to stay on top of. And I'm pretty sure I was on 43 Folders or some of the various different websites at the time, Inbox Zero being a thing that was like, okay, is that a desire? And I remember coming across, getting things done, and I picked up the book and it just really resonated with me. When I read that book I felt like, okay, this is a process that seemed to me to hit the goals that I wanted and could scale with the kind of things that I wanted to do. Now when I read it, there was a lot of references to paper files. And I'm a technologist, I mean, I've always been a technologist, I'm like, I'm not doing that. That's fine for others, but not for me. And so I looked around and actually I went and did the research to make sure I got this right. It was July 2008 when I bought my very first license to OmniFocus. So I've been using the software now for coming up on 16 years and have never used anything else. I've always felt like I wanted to be an expert at the tool that I use in OmniFocus, and I wanted to really focus on getting the system with getting things done. And so now I had heard of Omni Group before that I had used OmniGraffle, and OmniGraffle was a great app. I wasn't a power user of it in any way. I needed a solution for that kind of capability when I was on a Mac. And so I thought highly of The Omni Group themselves, and I never did do any of the kind of [inaudible 00:05:26] GTD stuff and OmniPlan, but I remember that being a thing. But no, I jumped right on OmniFocus in 2008.

Andrew J. Mason: So stinking cool. Jamie, I'd love, if you don't mind, a preview into your world, because you mentioned working there for over 30 years. 2008 I think is still a couple of years to spare there. What system were you using prior to GTD, OmniFocus and that kind of operating system for your brain? How were things being handled and did any of your peers happen to notice any difference after the fact?

Jamie Thinglestad: So I've been a CTO role for 30 years in different companies, but I would say that I was doing what a lot of people do for a while. I managed things through my email inbox. Frankly, I'd have things in my inbox and I'd tend to them, and then as I would deal with them, I'd delete them out. But my to-do list was for practical purposes, it was my email inbox. I never got the habit of emailing myself, which a lot of people start doing that. But I would do that and I would have lists that I would keep, but not in a consistent place, and certainly not with contexts associated with them. But I had kind of a task that was really in my inbox. So I don't know that anybody else would know. I think that GTD for me, I find GTD is something that is kind of an operating system for me, and it helps me do things better, but I don't necessarily try to advertise that to everybody else. So hopefully they saw just more calmness and more preparedness. Although I do tell people, I've told people over the years, I'm an avid practitioner of GTD and I keep copies of getting things done in my office and anybody on my team who is interested, I give them a copy and tell them I'm happy to talk more about how they want to use it in the future.

Andrew J. Mason: Fair enough. So nobody's coming up to you saying, "Man, Jamie, your smile is just brighter these days. Wow."

Jamie Thinglestad: No.

Andrew J. Mason: Not happening quite in that way. But I am curious though, what advice would you have for somebody who maybe finds themselves in that space of expanding roles? You're constantly having more and more, I can imagine, put on your plate over time. If somebody finds himself in that same sort of brain space where, hey, I need to be doing something to keep track of my ideas. I haven't really been doing anything. My system has been no system. What's a great first step for somebody like that?

Jamie Thinglestad: My first thing I would say is to keep expectations in check. I do think that people may have a thought that there's some magic key out there that when you just turn that key, everything's better. And the reality is that like anything, it takes time to adapt and make these systems work. And so I would recognize that you're making a big shift and appropriately look at that. And that's one of the reasons why I often refer to GTD, particularly as a life skill because I think it's something that I will carry through my whole life and I just work to get better at over time. And then the other thing I think is important is that I think there's multiple components to adopting a system. So there's the tools that you use to make the system work. There's the system itself that is kind of like, okay, maybe that's the way you want to structure your GTD methodology. And then I think very importantly, there's the stuff in the system, the things that you actually put in there. And one of the things that I've seen time and time again is if the stuff that's in your system is stuff you don't want to do, there's no system that's going to necessarily solve that. So making the activities be attractive the things that detract you, that's not a system issue. And so I tend to think that there's like, you got to look at the system, you got to look at the tools and the stuff in the system as three different components and make sure that when you're trying to solve or improve that you're not trying to solve system problems with the tool or that you're not trying to solve problems in your system or the fact that the stuff is not attractive to you, it's not interesting, don't try to solve that by changing your tool. So I think thinking of those as very different things is important. And for example, I've been using OmniFocus for 16 years, but I've radically revamped my system. I probably revamped my system every 18 months. And just like anybody, I've probably got a couple of things in my list that might've been added three years ago and I still haven't done it well, that that's not a fault of my system.

Andrew J. Mason: It's a really good distinction to make. And I think an important one too, one that speaks to the shiny app syndrome where you see a feature that kind of draws you off into a certain direction. I would love to hear maybe a bit more about what the nuts and bolts of your system kind as it stands today, looks like. Talk to me, more about what shows up in the inbox, maybe how things are structured for you. Is there a use of tags or perspectives for you? And just placing it kind in the overall ecosystem of what flows into it, what flows out of it? Just give us a little bit of the lay of the land there for you.

Jamie Thinglestad: So the system itself, so the tools that comprise my system, OmniFocus does sit right in the middle. So OmniFocus is kind of the connective tissue that makes that all work. But I use a lot of tools alongside OmniFocus. So one of the ones that I really like is Drafts. Drafts is a great capture tool. So if I just need to quickly jot down text, I don't want to think about, oh, where does it go? I just want to think about, let me get this text down. And so I'm going to pull up Drafts and just kind of capture. I do a lot with automation and shortcuts. So I use shortcuts to take templates that I create on task paper and then rehydrate those into new things inside of OmniFocus. I use SaneBox with the mail drop feature. One of the things that I recognize, it took me a long time to recognize this honestly, but there are certain emails that I get that are never processed as emails. They're always processed as actions. And so I route those completely around my mailbox and it goes directly into my OmniFocus inbox so that I'm never bothered with them in my email flow. They're just not email. They're actually a task. Additionally to that, I do use Siri. Siri Reminder Capture. I find that there are a lot of times when I choose to not listen to anything when I'm driving, and I use that as a mind sweep. And so just hammering off, remind me, remind me, remind me. And then the last two components of my system or the kind of tool chain is Agenda, which is an app that I use that is about note-taking but what I like about it is that it fundamentally, it's constrained around your calendar, so it's always contained to your calendar. And as a CTO, my day is my calendar. I mean, my calendar every day has dozens of events on it, and everything that's going to happen in that day is going to be driven by that calendar. And so being able to use Agenda where I don't have to think about it, I can just go like, okay, I'm in this meeting, it's time to take a note. I pop it open and it's there ready to go. That's kind of the last component. In terms of the system, I do have kind of categorical folders that map to my areas of focus. So I've got one for self, me, I've got one for family, I've got one for SPS, I've got one for hobbies, I've got one for our house. That's kind of how I match it. So I kind of think about my areas of responsibility and I map that directly to the folders themselves.

Andrew J. Mason: That's fantastic. Yeah. Do you use tags in any way?

Jamie Thinglestad: I do. I do. I was a big fan when we switched from context to tags in OmniFocus, it took me a little while and I would say tags is actually the area where I've revamped my system maybe more times than many other areas. And so like I mentioned, I have an Agenda tag and I expand that Agenda tag down hierarchically into a bunch of different categories and probably go as much as I go about four deep on that. For me, there are a lot of things that I'm doing that I need to be with a person to do. And so I put in a tag that is specifically for all the people that I work with frequently at the office and then I know, okay, I'm going to visit that tag anytime I have an interaction with that person. And so that I can put my waiting fors and my agendas all associated with that tag. But I have tried to keep them, I do find that I can get tag overload, and so I kind of visit my tags regularly and make sure am I using them? If I'm not using them, let's get rid of them. And one that I've kind of toggled on is having a today tag. I've had that. I continue to have it. I used to have a repeating tag, but thanks to OmniFocus for that too, I don't need that anymore because I can now have a perspective that's filtered on is repeating. So I don't need that tag anymore.

Andrew J. Mason: No, that's fantastic. Let's zoom out a little bit though. Talk to me a little bit more about what would make you, and I'll couch this question around a little bit of context with, somebody doesn't do kind of all the tweaking and all the system kind of management that you do. Well, first of all, with the sheer volume of stuff that you do, of course. But I have to believe there's a level of internally you want to see how far you can push yourself, and not to the point of burnout, but to the point of what am I truly capable of? And I always love to ask the question, what makes you passionate about being as productive as you possibly can? Where does that come from for you?

Jamie Thinglestad: Well, I mean, part of it is I like to do a lot of stuff. I've got a very busy and demanding job. We have family life, I've got hobbies. I like to do things. And so having a system just allows me to get more done. And by getting more done, I get to have more experiences and just kind of get more enjoyment out of that. So I mean, a little bit of it was I had to, because I think not having a system, just the old saying, right, your brain's for having ideas, not for storing them. And there's only so far that I could get without having more of a system to fall back on. However, I'll also add, and this is one, I think this is something that is worth revisiting. I go back to David Allen's thesis with getting things done, and he talks about mind like water and being very zen about being present. And I will say for the first few years for sure, I was focused on how do I get more productive? How do I drive efficiency in my system? And I would say in the last few years, I've really focused more on that aspect of how do I make sure that I can be present? How do I make sure that my brain isn't thinking about the stuff that's happening over here and not able to think about the stuff that's happening in front of me right now? And I mean, one of my favorite GTD examples is if we take a vacation, I can just go into my system and I punch a bunch of defer dates and I'm done. I am not worrying about anything. It's fine. I know exactly that when we come back I'm not going to have dropped anything. I'm not going to have to remember a bunch of stuff. It's just there. It's in my system. So I think that kind of mind like water thing is something that I believe gets lost in the kind of hunt for productivity when it's really about a hunt for kind of mindfulness and being present.

Andrew J. Mason: Yeah, well said. I mean, it feels like a superpower first. So you start to ask the question, what can I get done? What can I do? How far can I go? And just you speaking to what you were saying there just a second ago with the price that you paid and investing in getting the system set in a way that you can really dive into context and switch back out of context at a moment's notice, that doesn't come for free, but man, it's priceless. When you're sitting there and your son wants to play Pokemon or at story time with your daughter, and you can actually be there in that moment with them not thinking about, did I help fix somebody's laptop, about something that happened way earlier and needs to happen two weeks from now?

Jamie Thinglestad: Exactly.

Andrew J. Mason: Talk to me about automation. You mentioned shortcuts and automation playing a role. You kind of alluded a little bit to task paper and drafts and their interplay back and forth. I kind of get the sense that you mentioned templating has a slice to play. Anything in terms of a deeper dive into how you use automation in your tasks?

Jamie Thinglestad: Yeah, I do a lot with this. So obviously just the basic stuff, even of having repeating tasks and making sure that... I actually, for a number of years, I veered away from the idea of a tickler of that charm. I was like, no, I don't know if that's really the right term. But I actually think being able to just kind of put stuff out there that I don't have to think about and just think clearly about what the repeating task is. By the way, I think there's an unlock there that oftentimes people have the repeating task be the action to do the thing. And I think that oftentimes what I found is I just make the repeating task to create the project to do the thing so that I remove friction from the actual act, which allows me to use kind of repetition to my benefit. Because sometimes the repetition it is like if I got to do the work, but I can't do it right now, then how do I manage that? But I do use pretty robust automation around things like I publish a weekly newsletter and to publish that newsletter, there's probably about 17 to 18 different steps that I take. And I know them but having the automation and putting it into OmniFocus allows me to have all of the helper URLs right there. I don't have to go someplace else. It's just right there. And I can put my mind on autopilot and just go like, okay, what's the next thing? Oh yeah, the next thing is to do this. Almost every one of those then runs some shortcut or some script that I then use to connect other parts together. But that kind of automation is great. And I don't use a repeating project for that because one of the challenges with repeating projects is anything that I do to that project will then happen again. And one of the nice things about templates that you create just for one use is I can modify and change them, change dates, add things that might be special for one instance of that. But then I know that the next time I'm going to start with a brand new pristine project. I have some automation that people might think is funny, but I'm a member of a book club. And one of the things about being a member of a book club is you got to read the book by the date. And so I wrote an automation that just allows me to say, here's the name of the book, here's how many chapters it has, here's when I need that, here's when the meeting is, and then it calculates how many days do I have? And it puts every chapter in with a due date that says like, okay, here's your pacing for reading the book. And then it helps me make sure I get my books read on time. And then the other one that I think is kind of fun is holidays. So you look at something like Christmas, there's so much that happens around Christmas, and I kind of decomposed that after a while. I was like, okay, well really, there's five discrete projects that make up Christmas, and I have a template for each one of them. And so when the holidays come around, I run my automation that says Create the Christmas Projects. It creates all five projects, associates the right tags with everything. And then the very last item in those projects is update the project template for next year. And what I'm doing there is paying Jamie tomorrow with a little bit of benefit of like, okay, did I miss anything? Did anything change? Okay, let's update that so that next year I gain that benefit. Great one for that is file your taxes. It's like, I've got a template for that so that I can then say, okay, don't forget about that account. Well, I won't forget about it because I put it in the template and it's now part of the solution.

Andrew J. Mason: I love that idea though, to include a last step to iterate on what was already happening there. And it's so funny to me that, yeah, it's not a repeating project, but people are surprised that Christmas is coming again this year. Like, oh my gosh. But there it is. Oh no! It's like I had no idea, that was new information. Wow.

Jamie Thinglestad: Well, one of the things that I found helpful is I keep all those templates in drafts because I think the trick is you got to remove friction from the process of updating them as well. So keeping them in a place where, and I've got the link right to the draft, so at the end it's just you tap that link, drafts opens up, it's got the task paper template, make any changes that you want to make. You're done. You're ready. So making it really simple to do that I think is important.

Andrew J. Mason: Well, so I hear a little bit in your story, the agile methodology where it's just like iterate, do a little sprint, see how it works. Does it work for the system? That's great. Or if not, scrap it. Talk to me a little bit about was there anything along the course of your journey that as you look back, you're like, you know what? At the time I thought that was a really good idea for the system or the way to approach things, and in retrospect, maybe not. I learned from it. And so if somebody is kind of following along on their journey and they're a mile or two back, you can say, you know what? If that's you, just go ahead and just skip that part. You don't need to do that.

Jamie Thinglestad: Yeah, a hundred percent. I think one of the things that I learned, I think many people do this, but when I first set up the system using due dates as a way to drive action as opposed to being a true reflection of a due date. Just made up due dates that we're really there to try to create some semblance of order in your system, which can be incredibly off-putting, right? And so then all of a sudden you have these overdue tasks and you don't want to look at it because it just reminds you of all these kind of failed promises that you have out there. And so I think one of the things that I, and I actually, I remember I grabbed the OmniFocus field guide from MacSparky, which was a huge unlock because he's like, never use a due date unless it's an actual due date. Don't make due dates in your system unless they're true due dates. And then really focusing on defer dates. And that's become so much part of my life that I don't even know how I could use a system that doesn't support defer dates. That's just a core foundational capability. So I think this overusing due dates is definitely a mistake. I think getting into tags at a level of esoteric detail that represents maybe some OCD tendencies but doesn't really add value. So just reflecting on, am I using this tag? If I'm not using it, why am I setting it? Just be really careful about that. And then even I felt almost embarrassed about this as I'm like 16 years I've been doing GTD and I'm watching Meg Edwards, this amazing GTD coach do a thing on YouTube, and she's like, oh, make sure that you, in OmniFocus where the settings are there's a setting that says clean up inbox items, which I have and whenever I installed OmniFocus in July of 2008, I set that to when it has both a project and a tag. And I was like, well, of course it should have a project and a tag. And she's like, no, this should be set to either a project or a tag, and then explained why. And I was like, oh my gosh. I was like, this is a huge unlock. All of a sudden I'm like, right, why am I sitting here with a perspective for untagged meticulously adding tags to stuff that is never going to be used? It's not actionable yet. So I was like, oh, yeah, I went and changed that, and that actually caused me just that one setting-

Andrew J. Mason: It's the relief

Jamie Thinglestad: ... caused me to go, I deleted three or four tags from my system. I was like, I don't need these anymore because I was using my kind of meta tags to get them out of my inbox and allowed me to refactor stuff in a way that was like, oh, this is so much better. So it's small thing, but huge impact.

Andrew J. Mason: That's really interesting. For me, it's the opposite direction. And thank you for bringing that to my attention. I do think I have both of them checked myself right now, and it explains why you tag something that's an agenda item in your inbox and it doesn't go away. And you're like, you start twitching. Like, there needs to be a project attached to this and I don't know what it is, let's just talk to somebody. Do I want to build a project around asking somebody how their day was? Maybe.

Jamie Thinglestad: Exactly.

Andrew J. Mason: I really appreciate you spending this much time with us. I know that you're an incredibly busy person. I think that anybody that watches this podcast will see the testament to your ability to be present in the moment, even when there are things swirling around. So thank you for that gift. But if folks are interested in connecting with you or finding out more about what you're up to, how can they do that?

Jamie Thinglestad: Well, for sure the best way to do that is the newsletter that I publish. I publish a weekly newsletter called The Weekly Thing at weeklything.com. It's free. There's nothing commercial about it, it's a hobby of mine. It's where I share what I'm learning. So I think to have a career in technology is to have a career in learning. And so I want to share what I'm learning and what I'm kind of digging into. And I do that via The Weekly Thing. So if you sign up and subscribe there, you'll get everything that I find interesting or relevant.

Andrew J. Mason: That's fantastic. Jamie, thank you so much for your time. This has been a blast.

Jamie Thinglestad: Thank you.

Andrew J. Mason: Hey, and thank all of you for listening today, too. You can find us on Mastodon at theomnishow@omnigroup.com. You can also find out everything that's happening with The Omni Group at omnigroup.com/blog.